Holiday Packages in Winthrop, Massachusetts

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Tips for booking hotels in Winthrop

Gain useful insights to help choose a hotel in Winthrop. Data was last updated on Fri Dec 12 2025.
Cheapest month:November
Most expensive month:August
Average price in Winthrop:£126/night
Cheapest price found:£34/night
Cheapest day:Wednesday
Most expensive day:Thursday
£34 - £249
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£70 - £264
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Winthrop vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Fri Dec 12 2025.
Sheraton Boston Hotel
Sheraton Boston Hotel

Sheraton Boston Hotel

39 Dalton Street, Boston, MA, United States
0.0 mi from city centre
Pool
£1,154
Avg. per night
View Deal
Hyatt Regency Boston Harbor
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

101 Harborside Drive, Boston, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,112
Avg. per night
View Deal
The Colonnade Hotel
The Colonnade Hotel

The Colonnade Hotel

120 Huntington Avenue, Boston, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,237
Avg. per night
View Deal
Hyatt Regency Boston
Hyatt Regency Boston

Hyatt Regency Boston

1 Avenue de Lafayette, Boston, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,222
Avg. per night
View Deal
The Lenox
The Lenox

The Lenox

61 Exeter Street, Boston, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,504
Avg. per night
View Deal
The Kendall Hotel
The Kendall Hotel

The Kendall Hotel

350 Main Street, Cambridge, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,347
Avg. per night
View Deal
Hotel Aka Back Bay
Hotel Aka Back Bay

Hotel Aka Back Bay

154 Berkeley Street, Boston, MA, United States
0.0 mi from city centre
Free Wi-Fi
£1,462
Avg. per night
View Deal
W Boston
W Boston

W Boston

100 Stuart Street, Boston, MA, United States
0.0 mi from city centre
£1,379
Avg. per night
View Deal
See all

Where to stay in Winthrop

Utilise the map to find the perfect place to stay for your trip to Winthrop. There are 8 hotels to choose from in Winthrop.

FAQ about Winthrop holiday packages

Find answers to frequently asked questions Cheapflights users have about Winthrop holiday deals.

  • How much are vacation packages to Winthrop?

    The cheapest price of a Winthrop flight+hotel is currently £1,070.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Yes! Holidays on Cheapflights are designed to help users save money by bundling their flight, car rental, and hotel.

  • What other destinations does Winthrop have flight+hotel deals to?

    In addition to Winthrop, Cheapflights also offers holiday packages to Massachusetts

Other popular holiday deals in Massachusetts

Consider booking a Flight+Hotel in one of these other areas of Massachusetts.
Massachusetts holidays
Boston holidays
Salem holidays
Bedford holidays
Burlington holidays
Cambridge holidays
Peabody holidays
Springfield holidays
Quincy holidays
Waltham holidays
Worcester holidays